An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement
Publication type: Journal Article
Publication date: 2001-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Starting from commercially available naringenin (3), the flavanoids 8-prenylnaringenin (1) and 6-(1,1-dimethylallyl)naringenin (2) have been prepared in racemic form using prenyl ether 5 as a general intermediate. While a domino Claisen–Cope rearrangement of 5 was the key step in the synthesis of 1, the cytotoxic compound 2 was additionally secured via a europium(III)-catalyzed Claisen rearrangement of 5 at low temperature. Both 1 and 2 display strong estrogenic activities.
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Metrics
97
Total citations:
97
Citations from 2024:
2
(2.06%)
The most citing journal
Citations in journal:
8
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GOST
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Gester S. et al. An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement // Tetrahedron. 2001. Vol. 57. No. 6. pp. 1015-1018.
GOST all authors (up to 50)
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Gester S., METZ P., Zierau O., Vollmer G. An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement // Tetrahedron. 2001. Vol. 57. No. 6. pp. 1015-1018.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0040-4020(00)01078-4
UR - https://doi.org/10.1016/S0040-4020(00)01078-4
TI - An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement
T2 - Tetrahedron
AU - Gester, Sven
AU - METZ, PETER
AU - Zierau, Oliver
AU - Vollmer, Günter
PY - 2001
DA - 2001/02/01
PB - Elsevier
SP - 1015-1018
IS - 6
VL - 57
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2001_Gester,
author = {Sven Gester and PETER METZ and Oliver Zierau and Günter Vollmer},
title = {An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement},
journal = {Tetrahedron},
year = {2001},
volume = {57},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/S0040-4020(00)01078-4},
number = {6},
pages = {1015--1018},
doi = {10.1016/S0040-4020(00)01078-4}
}
Cite this
MLA
Copy
Gester, Sven, et al. “An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement.” Tetrahedron, vol. 57, no. 6, Feb. 2001, pp. 1015-1018. https://doi.org/10.1016/S0040-4020(00)01078-4.